HCID 178433821, compound → HCID 178433823, compound

HRID 2271457Notes

Reaction equation

HRID 2271457 reaction equation
[OH:1][C:2]1[C:7]([NH:8]/[N:9]=[C:10]2/[C:11]([CH3:26])=[N:12][N:13]([C:16]3[CH:25]=[CH:24][C:23]4[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=4[CH:17]=3)[C:14]/2=[O:15])=[CH:6][CH:5]=[CH:4][C:3]=1[C:27]1[CH:28]=[C:29]([C:32]([OH:34])=[O:33])[O:30][CH:31]=1>O1CCCC1>[CH2:2]([CH2:7][NH2:8])[OH:1].[CH2:2]([CH2:7][NH2:8])[OH:1].[OH:1][C:2]1[C:7]([NH:8]/[N:9]=[C:10]2/[C:11]([CH3:26])=[N:12][N:13]([C:16]3[CH:25]=[CH:24][C:23]4[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=4[CH:17]=3)[C:14]/2=[O:15])=[CH:6][CH:5]=[CH:4][C:3]=1[C:27]1[CH:28]=[C:29]([C:32]([OH:34])=[O:33])[O:30][CH:31]=1

Participants

3

Reactant 1

HCID 178433821HCID 178433821, compound

Product 1

HCID 178433823HCID 178433823, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Z)-4-(2-hydroxy-3-{N′-[3-methyl-5-oxo-1-(5,6,7,8-tetrahydro-naphthal-2-yl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-phenyl)-furan-2-carboxylic acid 22f (1.2 g, 2.6 mmol) was dissolved in 20 mL of tetrahydrofuran to form a dark red suspension. The reaction mixture was added with ethanolamine (399 mg, 6.5 mmol) to form a purple solution, and stirred for 6 hours at room temperature. A great quantity of the solid was precipitated from the solution, filtered, then the filter cake was washed with tetrahydrofuran (1 mL×3) and dried in vacuo to obtain the title compound (Z)-4-(2-hydroxy-3-{N′-[3-methyl-5-oxo-1-(5,6,7,8-tetrahydro-naphthal-2-yl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-phenyl)-furan-2-carboxylic acid bis-(ethanolamine) 22 (1.51 g, as a red solid) yield 72.8%.

Workup

  1. customto form a dark red suspension
  2. customto form a purple solution
  3. customA great quantity of the solid was precipitated from the solution
  4. filtrationfiltered
  5. washthe filter cake was washed with tetrahydrofuran (1 mL×3)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-535331dead354691abd4e1c8da33759c
Source dataset
uspto-grants-2015_09
Patent number
US09120762B2

Reaction notes

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